WO1997002274A1 - Production de nouveaux mono(di)thiophosphates, compositions comprenant ces derniers et procede d'application - Google Patents
Production de nouveaux mono(di)thiophosphates, compositions comprenant ces derniers et procede d'application Download PDFInfo
- Publication number
- WO1997002274A1 WO1997002274A1 PCT/RU1996/000174 RU9600174W WO9702274A1 WO 1997002274 A1 WO1997002274 A1 WO 1997002274A1 RU 9600174 W RU9600174 W RU 9600174W WO 9702274 A1 WO9702274 A1 WO 9702274A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mixture
- group containing
- synergistic
- methyl
- carbons
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 9
- 241000238631 Hexapoda Species 0.000 claims abstract description 11
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 230000002195 synergetic effect Effects 0.000 claims description 17
- 239000002917 insecticide Substances 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 5
- 241001674044 Blattodea Species 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 241000254173 Coleoptera Species 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 235000014633 carbohydrates Nutrition 0.000 claims description 3
- 235000005911 diet Nutrition 0.000 claims description 3
- 230000037213 diet Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 235000002333 black apple Nutrition 0.000 claims 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims 1
- 229960000490 permethrin Drugs 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000009193 crawling Effects 0.000 abstract 1
- 229910052760 oxygen Chemical group 0.000 abstract 1
- 239000001301 oxygen Chemical group 0.000 abstract 1
- 241000220225 Malus Species 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 235000021016 apples Nutrition 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 230000034994 death Effects 0.000 description 3
- 231100000517 death Toxicity 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- RLEWTHFVGOXXTN-UHFFFAOYSA-N 2,3-diethylphenol Chemical compound CCC1=CC=CC(O)=C1CC RLEWTHFVGOXXTN-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- -1 amyl-amyl Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003048 aphrodisiac agent Substances 0.000 description 1
- 230000002509 aphrodisiac effect Effects 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- 230000009916 joint effect Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 231100001224 moderate toxicity Toxicity 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- NIFIFKQPDTWWGU-UHFFFAOYSA-N pyrite Chemical compound [Fe+2].[S-][S-] NIFIFKQPDTWWGU-UHFFFAOYSA-N 0.000 description 1
- 229910052683 pyrite Inorganic materials 0.000 description 1
- 239000011028 pyrite Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Definitions
- shi ⁇ is ⁇ lzuem ⁇ g ⁇ in ⁇ e ⁇ a ⁇ a ⁇ ivny ⁇ ⁇ ma ⁇ ⁇ i ⁇ e ⁇ id ⁇ v, ⁇ ednaznachenny ⁇ for b ⁇ by with sinan ⁇ nymi le ⁇ ayuschimi nase ⁇ mymi (mu ⁇ and ⁇ ma ⁇ y) yavlyae ⁇ sya ⁇ i ⁇ e ⁇ nilbu ⁇ sid [I. ⁇ .Le ⁇ n ⁇ va, ⁇ . ⁇ .Slyn ⁇ , ⁇ g ⁇ imiya 1988, ⁇ ° 8, pp. 130-140].
- the intentional manufacture of pyroxide is carried out by the company Ziba-Gaigi (Switzerland). Similar insecticidal preparations based on mixed mixtures of this synergistic system and part of the process are detected
- synergistic insecticidal mixture ⁇ P ⁇ 0147064 rion ME2
- synergistic mixture in general as a general factor:
- ⁇ is an alkali group containing from 2 to 4 carbons
- ⁇ 1 is an alkali group containing from 1 to 2 carbons
- 0,0-diethyl- ⁇ - [( ⁇ -ethyloxycarbonyl- ⁇ -methyloxybenylmethyl) aminomethyl] dietophosphate, 0,0-diethyl- ⁇ - [( ⁇ -ethyloxycyclobenyl, amyl-amyl) 0-diethyl- ⁇ - [( ⁇ -methyl-oxoxylated- Economics ⁇ -isobutyl-oxylbenyl) aminomethyl] dietethyl, ⁇ _0 0,0-diethyl- ⁇ - [( ⁇ -methyl-amyl-nitrous-amyl -dipropyl- ⁇ - [( ⁇ -methyloxybenyl- ⁇ -methyloxybenylmethyl) aminomethy] mono 1 and 2, respectively.
- the claimed divergent (often) type of device may be used in combination with any environmentally friendly and auxiliary substances.
- an insecticidal preparation is obtained by dissolving a mixture of a spermethrin and a synergistic agent in an industrial device.
- ⁇ levy ⁇ is ⁇ y ⁇ aniy is ⁇ lzuyu ⁇ inse ⁇ itsidnuyu ⁇ m ⁇ zitsiyu as v ⁇ dn ⁇ g ⁇ ⁇ ab ⁇ cheg ⁇ ⁇ as ⁇ v ⁇ a
- ⁇ ig ⁇ vlyaem ⁇ g ⁇ ⁇ b ⁇ az ⁇ m follows: a mixture ⁇ e ⁇ me ⁇ ina and sine ⁇ gis ⁇ a ⁇ as ⁇ v ⁇ yayu ⁇ in ⁇ ganiches ⁇ m ⁇ as ⁇ v ⁇ i ⁇ ele, vv ⁇ dya ⁇ emuls ⁇ gen and ⁇ luchenny ⁇ ntsen ⁇ a ⁇ emulsion ⁇ azbavlyayu ⁇ v ⁇ d ⁇ y d ⁇ zhelaem ⁇ y ⁇ ntsen ⁇ atsii, ⁇ luchaya us ⁇ ychivuyu v ⁇ dnuyu emulsion.
- Non-hazardous insecticide mixes are applied with the use of the Hamilton sprinkler on the front of the imago of small flakes and 1 volume of tobacco. Taking into account the deaths of insects occurs after 24 hours for small flies and after 48 hours for synanthropic cockroaches.
- the degree of toxicity separates the average dose (SD 50 , ⁇ g / g), and the data on the death of the insects is processed by the method [P.I. 72-74].
- the degree of synergistic activity of the claimed compounds determines the value of the coefficient of the combined action (SD) of the synergistic mixture - at a ratio of 10% by weight:
- test experiments with a test without a system and experiments with a known syngress are put in place - a pyrotechnic test is standard.
- the invention may also include other variations in the scope of the invention.
- the invention is described in the paragraphs of the formula below. ⁇ ⁇ 97/02274 ⁇ / ⁇ 6 / 00174
- the intentional use of the invention provides for the production of new insecticidal preparations containing the claimed new derivatives (often).
- the invention may be used to combat the creeping and flying insects in the home and agriculture.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Organic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Cette invention concerne la production de nouveaux mono(di)thiophosphates correspondant à la formule générale (I) où R représente un groupe alkyle comportant de 2 à 4 atomes de carbone; R1 représente un groupe alkyle comportant de 1 à 2 atomes de carbone, un groupe aryle ou un groupe aryle substitué; R2 représente un groupe alkyle comportant de 1 à 4 atomes de carbone; X représente soufre ou oxygène. Cette invention concerne également la production de nouvelles préparations insecticides contenant ces nouveaux composés, et peut être utilisée dans la lutte contre les insectes volants et rampants, que ce soit dans les applications domestiques ou dans le domaine agricole.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU65372/96A AU6537296A (en) | 1995-06-30 | 1996-06-28 | Novel derivatives of di(mono)thiophosphates, a composition containing them and a method of using them |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU95111335/04A RU2087477C1 (ru) | 1995-06-30 | 1995-06-30 | 0,0-диалкил-s-[(n-алкокси(арокси)карбонил-n-алкоксикарбонилалкил)аминометил]ди(моно)тиофосфаты, проявляющие синергистическое действие к периметру в отношении комнатных мух и синатропных тараканов |
RU95111335 | 1995-06-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997002274A1 true WO1997002274A1 (fr) | 1997-01-23 |
Family
ID=20169633
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/RU1996/000174 WO1997002274A1 (fr) | 1995-06-30 | 1996-06-28 | Production de nouveaux mono(di)thiophosphates, compositions comprenant ces derniers et procede d'application |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU6537296A (fr) |
RU (1) | RU2087477C1 (fr) |
WO (1) | WO1997002274A1 (fr) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1424705A (en) * | 1972-04-27 | 1976-02-11 | Ciba Geigy Ag | Pesticidal dithiophoshphoric acid esters |
GB2039487A (en) * | 1978-12-14 | 1980-08-13 | Philagro Sa | New fungicidal derivatives of N- phenyl-N-(alkoxycarbonylalkyl) -acetamide phosphorodithioates |
US4231782A (en) * | 1978-11-03 | 1980-11-04 | Monsanto Company | N-Carbobenzoxy-N-phosphonomethylglycine thioesters |
EP0064670A1 (fr) * | 1981-05-02 | 1982-11-17 | Hoechst Aktiengesellschaft | Agents pesticides |
US4362722A (en) * | 1979-05-11 | 1982-12-07 | Ici Australia Limited | Synergistic tickicidal compositions containing organophosphorus compounds and cyclopropane carboxylates |
-
1995
- 1995-06-30 RU RU95111335/04A patent/RU2087477C1/ru not_active IP Right Cessation
-
1996
- 1996-06-28 WO PCT/RU1996/000174 patent/WO1997002274A1/fr active Application Filing
- 1996-06-28 AU AU65372/96A patent/AU6537296A/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1424705A (en) * | 1972-04-27 | 1976-02-11 | Ciba Geigy Ag | Pesticidal dithiophoshphoric acid esters |
US4231782A (en) * | 1978-11-03 | 1980-11-04 | Monsanto Company | N-Carbobenzoxy-N-phosphonomethylglycine thioesters |
GB2039487A (en) * | 1978-12-14 | 1980-08-13 | Philagro Sa | New fungicidal derivatives of N- phenyl-N-(alkoxycarbonylalkyl) -acetamide phosphorodithioates |
US4362722A (en) * | 1979-05-11 | 1982-12-07 | Ici Australia Limited | Synergistic tickicidal compositions containing organophosphorus compounds and cyclopropane carboxylates |
EP0064670A1 (fr) * | 1981-05-02 | 1982-11-17 | Hoechst Aktiengesellschaft | Agents pesticides |
Also Published As
Publication number | Publication date |
---|---|
RU95111335A (ru) | 1996-11-20 |
AU6537296A (en) | 1997-02-05 |
RU2087477C1 (ru) | 1997-08-20 |
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